My lathe is probably my oldest machine. Not sure how old, I think it was shop built by an aircraft company because of the tag on it. Haven't found another one like it on any of the old tool forums. 19 inch swing, 8 foot bed and about 68 inch turning length. Takes a #4 Morse taper in the tail stock. I added the variable speed motor.

Here it is when I first moved in to my current home. I had to turn some little thing for a friend and just turned the lathe by hand since the power wasn't ready yet. Yeah, there is a little three leg stool I made at my old place before we moved.

Well I went off with the above bench fixture" (the "whatyoumacallit") before I noticed what the actual title of this discussion is, the question "what is your oldest machine?".  So here's our oldest by far, probably not verifiable but the Mosers told me that this machine dates to the late 1790s, literally a contemporary of Thomas Jefferson.  And since the original shop was established in Lynchburg, VA, just seventy miles from Charlottesville and Monticello...who knows?  Anyway, here are pictures of our oldest machine.  We think that the machine was retrofit for the electric motor in about 1915-1917; before that it most likely was driven by a water or steam powered line shaft.

Ron Southard said:

Okay, here's a set of pictures of a 1920s bench fixture

My old machinery are a Darra James 218 and a Walker Turner L952 Lathe and a 1940 Walker Turner DP

 Plus I have a hand drill from when Black and Decker was a good company

That drill will tear both your arms off if it gets away from you.

My oldest hand tool is not currently a user

It was used to hew the oak beams in my home when it was built.  Yes, this very one.  It's the only tool that survived all these years  (about 250 of them) in the building, through all the owners.  

I think mine is a small jointah, from 1892but it is a cordless model......

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Planer? I'm the 'planer', and these are what I use...

My oldest machine is this Syracuse Disk Sander which was manufactured somewhere between 1918 and 1922 (I think).  I just acquired it at auction and I'm very pleased with how complete the piece is.  To my knowledge, the only missing piece is the mitre guage and the only aftermarket pieces are the table adjustment bolts.

I have a Bentel planer from the mid 70's, 1870's.  Next would be a Bentel jointer from the 1880's, plus a couple Frank Clement machines from then.